可见光诱导的有机光催化和单线态氧引发的 1,4-二氢吡啶、C-3 官能化螺[吲哚啉-3,4'-吡啶]和 C-11 官能化螺[茚并-[1,2-]喹喔啉-11,4'-吡啶]的串联构建。

Visible-light-induced organophotocatalytic and singlet oxygen-initiated domino construction of 1,4-dihydropyridines, C-3 functionalized spiro[indoline-3,4'-pyridines] and C-11 functionalized spiro[indeno-[1,2-]quinoxaline-11,4'-pyridines].

机构信息

School of Applied Material Sciences, Centre for Applied Chemistry, Central University of Gujarat, Gandhinagar-382030, India.

Asymmetric Synthesis and Catalysis Laboratory, Department of Chemistry, Central University of Tamil Nadu (CUTN), Tiruvarur-610 005, India.

出版信息

Org Biomol Chem. 2023 Feb 15;21(7):1518-1530. doi: 10.1039/d3ob00043e.

DOI:10.1039/d3ob00043e

PMID:36695344

Abstract

A highly efficient pot, atom, and step economical method for the construction of pharmacologically potent structurally functionalized 1,4-dihydropyridines, quaternary centered C-3 functionalized spiro[indoline-3,4'-pyridines], and C-11 functionalized spiro[indeno[1,2-]quinoxaline-11,4'-pyridines] rose bengal photoredox catalysis under blue LED irradiation in an aqueous medium at room temperature has been developed. The products were isolated in excellent yields within a short reaction time for a variety of functional groups under transition metal- and ligand-free energy-efficient conditions in a green solvent system with high reaction mass efficiency and process mass intensity, which are the key advantages of the current work.

摘要

一种高效的锅、原子和步骤经济方法，用于构建具有药理活性的结构功能化 1,4-二氢吡啶、季中心 C-3 功能化螺[吲哚啉-3,4'-吡啶]和 C-11 功能化螺[茚并[1,2-]喹喔啉-11,4'-吡啶]，在室温下在水介质中在蓝光 LED 照射下，使用 Rose Bengal 光氧化还原催化进行。在绿色溶剂体系中，在无过渡金属和配体、节能条件下，以高反应质量效率和过程质量强度为关键优势，针对各种功能基团，在短反应时间内以优异的收率分离出产物。